V0627

Valinomycin

≥98% (TLC), ≥90% (HPLC)

• Synonym(e): [(D-Val-L-Lac-Val-D-HyV)(3)](cycl.) (L-Lac: L-Milchsäure, D-HyV: D-α-Hydroxy-isovaleriansäure)
• Empirische Formel (Hill-System): C₅₄H₉₀N₆O₁₈
• CAS-Nummer: 2001-95-8
• Molekulargewicht: 1111.32
• Beilstein: 78657
• EG-Nummer: 217-896-6
• MDL-Nummer: MFCD00005114
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24900697
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 300
• Assay: ≥90% (HPLC); ≥98% (TLC)
• Form: powder
• Lagerbedingungen: (Keep container tightly closed in a dry and well-ventilated place.)
• Farbe: white
• Löslichkeit: DMSO: ≥50 mg/mL; H₂O: insoluble
• Wirkungsspektrum von Antibiotika: Gram-positive bacteria; parasites; viruses
• Wirkungsweise: cell membrane | interferes
• Lagertemp.: 2-8°C
• SMILES String: CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
• InChI: 1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1
• InChIKey: FCFNRCROJUBPLU-RPUZOQEISA-N

Beschreibung

Allgemeine Beschreibung

Chemical structure: peptide

Valinomycin is a cyclic peptide, which contains d-valine, d-α-hydroxyvaleric acid, l-valine, and l-lactic acid in the sequential order of cyclo-[(l-Val-d-Hyv-d-Val-l-Lac)₃].

Valinomycin, a nonribosomal peptide (NRP), is proposed to have a structure of a 24-membered cyclic peptide cyclo-(d-α-hydroxyisovaleryl-d-valyl-l-lactyl-l-valyl)2. It exhibits antitumor properties and plays a major role as a mitophagy activator. Initially isolated as an antibiotic compound, valinomycin has demonstrated antibacterial activity against Mycobacterium tuberculosis. Moreover, it has been identified as a potent antiviral agent against a wide spectrum of viruses, including human coronavirus, bunyavirus, enterovirus, and flavivirus.

Anwendung

Valinomycin has been used:

• to equilibrate intracellular pH and extracellular pH of 5 (and 6-)-carboxyfluorescein succinimidyl ester (cFSE) in Escherichia coli strain B23
• as an ionophore to equilibrate intracellular pH and extracellular pH of lactic acid bacteria (LAB) strains
• to establish the desired pH for acid-base transition and formation of K⁺-valinomycin diffusion potential

Biochem./physiol. Wirkung

K⁺-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.

Valinomycin selectively transfers alkali metal ions via biological and synthetic membranes. The formation of a metal ion-peptide complex contributes to this ion-transporting. Valinomycin can create stable complexes with potassium, rubidium, and cesium (K⁺, Rb⁺, and Cs⁺) .

Verpackung

10MG,25MG,100MG,500MG

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H300 + H310
• P-Sätze: P262 - P264 - P280 - P301 + P310 - P302 + P352 + P310 - P361 + P364
• Gefahreneinstufungen: Acute Tox. 1 Dermal - Acute Tox. 1 Oral
• Lagerklassenschlüssel: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges